Synthesis of 3-(Quinazolin-4-yl)propionic Acids via an Acid-Catalyzed Rearrangement of 4-Oxobutyronitriles

International Journal of Molecular Sciences 2026 Open access

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Authors: Nicolai A. Aksenov, Alexander E. Kurlikov, Alexander P. Barbolin, Polina S. Karaseva, Milena M. Baziyants, Elizabeth A. Glotova, Igor A. Kurenkov, Dmitrii A. Aksenov, Alexander V. Aksenov
DOI: 10.3390/ijms27093903
Cited by: 1
References: 39

Abstract

-toluenesulfonic acid (TsOH) undergo an unusual rearrangement providing access to a range of 3-(quinazolin-4-yl)propionic acids that have been poorly represented in the literature, with only a few isolated examples known to date. The reaction demonstrates a new route to the quinazoline core through transfer of the nitrile group nitrogen, mediated through the formation of a pyrrolidine cycle. The availability of 4-oxobutyronitrile precursors-2'-aminochacones-provides high variability of substituents in the required positions of product. The transformation is general and can be extended to the preparation of 2-substituted 3-(quinazolin-4-yl)propionic acids through preliminary acylation or to the synthesis of 4-(quinazolin-4-yl)butyric acids.

Fields of Study & Subjects

Quinazolinone synthesis and applications Synthesis and bioactivity of alkaloids Multicomponent Synthesis of Heterocycles

Publication details

Journal / source
International Journal of Molecular Sciences
Publisher
MDPI AG
Volume
27
Issue
9
Pages
3903–3903
Publication date
28 April 2026
Language
EN